6118-33-8Relevant articles and documents
Synthesis and characterization of novel color chemosensors based on azo dyes for possible application in opioid pharmacology
Genady, Afaf R.
, p. 1134 - 1143 (2010)
(Chemical Equation Presented) An applicable strategy of chemical labeling of morphine (M) and 6-acetyl morphine (6-AM) using diazonium salts is described. M or 6-AM was coupled with aryl diazoinum salts to give morphine azo dyes. The coupling of the diazotized 4,4′-diaminostilbene with M or 6-AM in ratio 1:2 gave stilbene-based azo dyes containing two M or 6-AM units, respectively. Diazotization of 5-(p-aminophenyl)-10,15,20-triphenylporphyrin and subsequent azo coupling of the diazoniun salt with M and with 6-AM was our route to get highly fluorescent morphine dyes. The resulting dyes can exist in two possible tautomeric structures, azo and hydrazone, stabilized to a significant extent by intramolecular H-bonding. It was shown that these dyes exists predominantly or exclusively in their hydrazone form. This conclusion is drawn from the lack of a distinct band in the 380-420 nm region of the absorption spectra (a region in which the long wavelength absorption band for the azo-form is observed), together with results of NMR studies in deuterated DMSO. The tautomeric properties of the compounds were judged by density functional calculations at the B3LYP/6-31G* and B3LYP/6-31G** levels. The analysis of spiked compounds in human urine samples was studied by capillary electrophoresis (CE) with UV-fluorescence photo-diode array detectors.
Novel analogs of sulfasalazine as system xc ? antiporter inhibitors: Insights from the molecular modeling studies
Patel, Dhavalkumar,Kharkar, Prashant S.,Gandhi, Neha S.,Kaur, Ekjot,Dutt, Shilpee,Nandave, Mukesh
, p. 758 - 777 (2019/06/24)
System xc ? (Sxc ?), a cystine-glutamate antiporter, is established as an interesting target for the treatment of several pathologies including epileptic seizures, glioma, neurodegenerative diseases, and multiple sclerosis. Erastin, sorafenib, and sulfasalazine (SSZ) are a few of the established inhibitors of Sxc ?. However, its pharmacological inhibition with novel and potent agents is still very much required due to potential issues, for example, potency, bioavailability, and blood–brain barrier (BBB) permeability, with the current lead molecules such as SSZ. Therefore, in this study, we report the synthesis and structure–activity relationships (SAR) of SSZ derivatives along with molecular docking and dynamics simulations using the developed homology model of xCT chain of Sxc ? antiporter. The generated homology model attempted to address the limitations of previously reported comparative protein models, thereby increasing the confidence in the computational modeling studies. The main objective of the present study was to derive a suitable lead structure from SSZ eliminating its potential issues for the treatment of glioblastoma multiforme (GBM), a deadly and malignant grade IV astrocytoma. The designed compounds with favorable Sxc ? inhibitory activity following in vitro Sxc ? inhibition studies, showed moderately potent cytotoxicity in patient-derived human glioblastoma cells, thereby generating potential interest in these compounds. The xCT-ligand model can be further optimized in search of potent lead molecules for novel drug discovery and development studies.
Synthesis and anti-oxidant evaluation of some novel sulfa drugs
Gouda, Moustafa A.,Hussein, Belal H.M.
, p. 1425 - 1432 (2017/12/28)
Background: Curcumins were reported to possess anti-inflammatory and antiangiogenic. Furthermore, Curcumin is a very potent free radical scavenger than vitamin E. Moreover, cyanoacetamides were reported to possess, antimicrobial antifungal, insulin releasing, antiinflammatory and antitumor. Thus the present study focuses on the synthesis of some novel structure hybrids incorporating either curcumin or cyanoacetamide with sulphonamide, aiming to reach a more potent antioxidant agent. Methods: 4-arylazoenol derivatives 12-16 and E-hydrazo derivatives 19-23 were prepared and their structure was confirmed by variable spectra analysis. The newly synthesized compounds were screened for their antioxidant activity using ABTS and Bleomycin-dependent DNA damage methods. Results: Coupling of the diazonium salts 7-11 of different sulpha drugs with curcumin 1 or with cyanoacetamide 18 afforded the corresponding 4-arylazoenol derivatives 12-16 and E-hydrazo derivatives 19-23. Among all the synthesized compounds, 12-16, 18, 20 and 22 were the most potent antioxidant compounds. Conclusion: The objective of the present study was to synthesize and evaluate the antioxidant activity of some novel sulfonamides structure hybrids incorporating either curcumin or N-[4- (aminosulfonyl) phenyl]-2-cyanoacetamide moiety with the hope of discovering new structure serving as antioxidant agent. The data showed clearly that most of compounds displayed good in vitro antioxidant activities.
